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Q.29.

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Organic Chemistry
Found in: Page 128

Short Answer

Question: Draw a chair conformation of cyclohexane with one group and one group that fits each description.

  1. a 1,1-disubstituted cyclohexane with an axial group
  2. a cis-1,2-disubstituted cyclohexane with an axial group
  3. a trans-1,3-disubstituted cyclohexane with an equatorial group
  4. a trans-1,4-disubstituted cyclohexane with an equatorial group

Answer

a.

b.

c.

d.

See the step by step solution

Step by Step Solution

Step 1: Conformational isomers

The stereoisomers that are easily convertible into one another by rotating about the carbon-carbon sigma bond are called conformational isomers.

These are further represented as staggered and eclipsed conformations.

Step 2: The chair conformations of cyclohexane with one ethyl and one methyl group

a. The structure of 1,1-disubstituted cyclohexane with an axial ethyl group is shown in the structure below:

1,1-disubstituted cyclohexane

b. The structure of cis-1,2 disubstituted cyclohexane with an axial methyl group is shown below:

Cis-1,4-disubstituted

The ethyl group in the above structure is in the equatorial position.

c. The trans 1,3 disubstituted cyclohexane with an equatorial methyl group is shown in the following structure:

Trans-1,3-disubstituted

In the above structure, the methyl group is now present at the equatorial position, and the ethyl group is present at the axial position.

d. The trans-1,4 disubstituted cyclohexane with an equatorial ethyl group is shown in the structure below:

Trans-1,4-disubstituted

The ethyl group, as well as the methyl group in the above structure, are present at equatorial positions.

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